Cyanamide → Methyl N-cyanobutanimidate

HRID 1197574Notes

Reaction equation

HRID 1197574 reaction equation
Cl.[C:2](=[NH:8])([O:6][CH3:7])[CH2:3][CH2:4][CH3:5].[N:9]#[C:10]N.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>>[C:10]([N:8]=[C:2]([O:6][CH3:7])[CH2:3][CH2:4][CH3:5])#[N:9]

Participants

4

Reactant 3

HCID 9864CyanamideHCID 24243Trisodium PhosphateHCID 12657464Methyl butanimidate--hydrogen chloride (1/1)

Product 1

HCID 15477524Methyl N-cyanobutanimidateYield 87.4%

Procedure

The methyl butyrimidate salt from Example 1 (322 g, 2.34 mol) was dissolved in a 50% aqueous solution of cyanamide (236 g, 2.81 mol) and cooled in an ice-bath. Dibasic sodium phosphate (164 g, 1.15 mol) was added to the reaction mixture in portions over a period of 1 hour. The resulting suspension was stirred at room temperature for 2 hours and the liquid decanted from the reaction mixture. The remaining solid was diluted with water (2 L) and extracted with ether (3×600 mL). The combined organic layers were washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue distilled under high vacuum to afford 258 g of methyl N-cyanobutyrimidate. MS (DEI) 127 (M+1).

Workup

  1. temperaturecooled in an ice-bath
  2. customthe liquid decanted from the reaction mixture
  3. additionThe remaining solid was diluted with water (2 L)
  4. extractionextracted with ether (3×600 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. distillationthe residue distilled under high vacuum

Sources & evidence

ORD record
ord-f82018d76c804e358bf1da216ff4b1fa
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

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